AR128043A1 - SALTS AND SOLID FORMS OF AN FGFR INHIBITOR AND PROCESSES FOR THEIR PREPARATION - Google Patents
SALTS AND SOLID FORMS OF AN FGFR INHIBITOR AND PROCESSES FOR THEIR PREPARATIONInfo
- Publication number
- AR128043A1 AR128043A1 ARP220103523A ARP220103523A AR128043A1 AR 128043 A1 AR128043 A1 AR 128043A1 AR P220103523 A ARP220103523 A AR P220103523A AR P220103523 A ARP220103523 A AR P220103523A AR 128043 A1 AR128043 A1 AR 128043A1
- Authority
- AR
- Argentina
- Prior art keywords
- acid
- salt
- formula
- salts
- solid form
- Prior art date
Links
- 239000007787 solid Substances 0.000 title abstract 7
- 238000000034 method Methods 0.000 title abstract 3
- 229940125829 fibroblast growth factor receptor inhibitor Drugs 0.000 title abstract 2
- 150000003839 salts Chemical group 0.000 abstract 8
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 229940125904 compound 1 Drugs 0.000 abstract 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 abstract 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 abstract 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 abstract 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 abstract 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 abstract 1
- ZBHJWDKPRTVNKG-VQTJNVASSA-N CC1=C(C=CC=C1C)C1=C(C=C2C(=N1)C(=NN2)C=1C=CC(=NC=1)N1C[C@H]2N(CC1)C[C@@H](C2)O)OC Chemical compound CC1=C(C=CC=C1C)C1=C(C=C2C(=N1)C(=NN2)C=1C=CC(=NC=1)N1C[C@H]2N(CC1)C[C@@H](C2)O)OC ZBHJWDKPRTVNKG-VQTJNVASSA-N 0.000 abstract 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 abstract 1
- 102000004190 Enzymes Human genes 0.000 abstract 1
- 108090000790 Enzymes Proteins 0.000 abstract 1
- 108091008794 FGF receptors Proteins 0.000 abstract 1
- 102100027842 Fibroblast growth factor receptor 3 Human genes 0.000 abstract 1
- 101710182396 Fibroblast growth factor receptor 3 Proteins 0.000 abstract 1
- 206010028980 Neoplasm Diseases 0.000 abstract 1
- 239000001361 adipic acid Substances 0.000 abstract 1
- 235000011037 adipic acid Nutrition 0.000 abstract 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 abstract 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 abstract 1
- 201000011510 cancer Diseases 0.000 abstract 1
- 229940125782 compound 2 Drugs 0.000 abstract 1
- 150000001875 compounds Chemical group 0.000 abstract 1
- 201000010099 disease Diseases 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 102000052178 fibroblast growth factor receptor activity proteins Human genes 0.000 abstract 1
- 239000001530 fumaric acid Substances 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 abstract 1
- 239000011976 maleic acid Substances 0.000 abstract 1
- 239000001630 malic acid Substances 0.000 abstract 1
- 235000011090 malic acid Nutrition 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 230000001404 mediated effect Effects 0.000 abstract 1
- 229940098779 methanesulfonic acid Drugs 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000546 pharmaceutical excipient Substances 0.000 abstract 1
- 239000001384 succinic acid Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/4985—Pyrazines or piperazines ortho- or peri-condensed with heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Abstract
La presente invención se refiere a sales y formas sólidas del inhibidor de FGFR (7R,8aS)-2-(5-(5-(2,3-dimetilfenil)-6-metoxi-1H-pirazolo[4,3-b]piridin-3-il)piridin-2-il)octahidropirrolo[1,2-a]pirazin-7-ol, e incluye métodos para su preparación, en donde los compuestos, las sales y las formas sólidas son útiles en el tratamiento de enfermedades mediadas por FGFR, tales como el cáncer. Reivindicación 1: Una forma sólida del Compuesto 1 con la fórmula: (1), caracterizada porque la forma sólida es cristalina. Reivindicación 17: Una sal caracterizada porque es una sal de adición de ácido del Compuesto 1, que tiene la estructura: de fórmula (1), en donde el ácido es ácido fosfórico, ácido clorhídrico, ácido L-tartárico, ácido malónico, ácido metanosulfónico, ácido adípico, ácido fumárico, ácido maleico, ácido málico o ácido succínico. Reivindicación 82: Un proceso para preparar el Compuesto 1 con la fórmula: (1), o una sal de este, caracterizado porque comprende: desproteger el Compuesto 2 con la fórmula: (2), o una sal de este, con A1, en donde A1 es un ácido. Reivindicación 117: Una composición farmacéutica caracterizada porque comprende una forma sólida de cualquiera de las reivindicaciones 1 - 16, o una sal de cualquiera de las reivindicaciones 17 - 81, y un portador o excipiente farmacéuticamente aceptable. Reivindicación 118: Un método para inhibir una enzima FGFR3, caracterizado porque comprende poner en contacto una forma sólida de cualquiera de las reivindicaciones 1 - 16 o una sal de cualquiera de las reivindicaciones 17 - 81 con dicha enzima.The present invention relates to salts and solid forms of the FGFR inhibitor (7R,8aS)-2-(5-(5-(2,3-dimethylphenyl)-6-methoxy-1H-pyrazolo[4,3-b] pyridin-3-yl)pyridin-2-yl)octahydropyrrolo[1,2-a]pyrazin-7-ol, and includes methods for its preparation, where the compounds, salts and solid forms are useful in the treatment of FGFR-mediated diseases, such as cancer. Claim 1: A solid form of Compound 1 with the formula: (1), characterized in that the solid form is crystalline. Claim 17: A salt characterized in that it is an acid addition salt of Compound 1, having the structure: of formula (1), wherein the acid is phosphoric acid, hydrochloric acid, L-tartaric acid, malonic acid, methanesulfonic acid , adipic acid, fumaric acid, maleic acid, malic acid or succinic acid. Claim 82: A process for preparing Compound 1 with the formula: (1), or a salt thereof, characterized in that it comprises: deprotecting Compound 2 with the formula: (2), or a salt thereof, with A1, in where A1 is an acid. Claim 117: A pharmaceutical composition characterized in that it comprises a solid form of any of claims 1 - 16, or a salt of any of claims 17 - 81, and a pharmaceutically acceptable carrier or excipient. Claim 118: A method for inhibiting an FGFR3 enzyme, characterized in that it comprises contacting a solid form of any of claims 1-16 or a salt of any of claims 17-81 with said enzyme.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US202163292628P | 2021-12-22 | 2021-12-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR128043A1 true AR128043A1 (en) | 2024-03-20 |
Family
ID=85172903
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP220103523A AR128043A1 (en) | 2021-12-22 | 2022-12-21 | SALTS AND SOLID FORMS OF AN FGFR INHIBITOR AND PROCESSES FOR THEIR PREPARATION |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US20230192722A1 (en) |
| EP (1) | EP4452982A1 (en) |
| JP (1) | JP2025500466A (en) |
| KR (1) | KR20240136984A (en) |
| CN (1) | CN118660889A (en) |
| AR (1) | AR128043A1 (en) |
| AU (1) | AU2022418585A1 (en) |
| CA (1) | CA3244187A1 (en) |
| CL (1) | CL2024001873A1 (en) |
| CO (1) | CO2024009568A2 (en) |
| CR (1) | CR20240297A (en) |
| IL (1) | IL313735A (en) |
| MX (1) | MX2024007951A (en) |
| PE (1) | PE20250776A1 (en) |
| TW (1) | TW202340215A (en) |
| WO (1) | WO2023122134A1 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2021067374A1 (en) | 2019-10-01 | 2021-04-08 | Incyte Corporation | Bicyclic heterocycles as fgfr inhibitors |
| CR20230467A (en) | 2021-03-10 | 2024-02-20 | Jnana Therapeutics Inc | SMALL MOLECULE INHIBITORS OF MAMMALIAN SLC6A19 FUNCTION |
| CA3220155A1 (en) | 2021-06-09 | 2022-12-15 | Incyte Corporation | Tricyclic heterocycles as fgfr inhibitors |
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| US6133031A (en) | 1999-08-19 | 2000-10-17 | Isis Pharmaceuticals Inc. | Antisense inhibition of focal adhesion kinase expression |
| GB9905075D0 (en) | 1999-03-06 | 1999-04-28 | Zeneca Ltd | Chemical compounds |
| GB0004890D0 (en) | 2000-03-01 | 2000-04-19 | Astrazeneca Uk Ltd | Chemical compounds |
| KR100786927B1 (en) | 2000-06-28 | 2007-12-17 | 스미스클라인비이참피이엘시이 | Wet Grinding Method |
| HUP0401982A3 (en) | 2001-09-19 | 2012-09-28 | Aventis Pharma Sa | Indolizine derivates, process for their preparation and pharmaceutical compositions containing the compounds |
| HU230798B1 (en) | 2001-10-30 | 2018-06-28 | Novartis Ag | Staurosporine derivatives as inhibitors of flt3 receptor tyrosine kinase activity |
| EP1456652A4 (en) | 2001-11-13 | 2005-11-02 | Dana Farber Cancer Inst Inc | AGENTS MODULATING IMMUNE CELL ACTIVITY AND METHODS OF USE THEREOF |
| ES2251677T3 (en) | 2002-01-22 | 2006-05-01 | Warner-Lambert Company Llc | 2- (PIRIDIN-2-ILAMINO) -PIRIDO (2,3-D) PIRIMIDIN-7-ONAS. |
| PE20040522A1 (en) | 2002-05-29 | 2004-09-28 | Novartis Ag | DIARYLUREA DERIVATIVES DEPENDENT ON PROTEIN KINASE |
| GB0215676D0 (en) | 2002-07-05 | 2002-08-14 | Novartis Ag | Organic compounds |
| TWI335913B (en) | 2002-11-15 | 2011-01-11 | Vertex Pharma | Diaminotriazoles useful as inhibitors of protein kinases |
| UA80767C2 (en) | 2002-12-20 | 2007-10-25 | Pfizer Prod Inc | Pyrimidine derivatives for the treatment of abnormal cell growth |
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| UA128453C2 (en) | 2018-03-30 | 2024-07-17 | Інсайт Корпорейшн | HETEROCYCLIC COMPOUNDS AS IMMUNOMODULATORS |
| PL3790877T3 (en) | 2018-05-11 | 2023-06-12 | Incyte Corporation | Tetrahydro-imidazo[4,5-c]pyridine derivatives as pd-l1 immunomodulators |
| WO2021076602A1 (en) * | 2019-10-14 | 2021-04-22 | Incyte Corporation | Bicyclic heterocycles as fgfr inhibitors |
-
2022
- 2022-12-21 JP JP2024538174A patent/JP2025500466A/en active Pending
- 2022-12-21 IL IL313735A patent/IL313735A/en unknown
- 2022-12-21 US US18/085,814 patent/US20230192722A1/en active Pending
- 2022-12-21 KR KR1020247024528A patent/KR20240136984A/en active Pending
- 2022-12-21 WO PCT/US2022/053582 patent/WO2023122134A1/en not_active Ceased
- 2022-12-21 CN CN202280091209.6A patent/CN118660889A/en active Pending
- 2022-12-21 AU AU2022418585A patent/AU2022418585A1/en active Pending
- 2022-12-21 AR ARP220103523A patent/AR128043A1/en unknown
- 2022-12-21 EP EP22854263.5A patent/EP4452982A1/en active Pending
- 2022-12-21 CR CR20240297A patent/CR20240297A/en unknown
- 2022-12-21 PE PE2024001456A patent/PE20250776A1/en unknown
- 2022-12-21 MX MX2024007951A patent/MX2024007951A/en unknown
- 2022-12-21 CA CA3244187A patent/CA3244187A1/en active Pending
- 2022-12-21 TW TW111149106A patent/TW202340215A/en unknown
-
2024
- 2024-06-19 CL CL2024001873A patent/CL2024001873A1/en unknown
- 2024-07-19 CO CONC2024/0009568A patent/CO2024009568A2/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN118660889A (en) | 2024-09-17 |
| CR20240297A (en) | 2024-09-18 |
| JP2025500466A (en) | 2025-01-09 |
| AU2022418585A1 (en) | 2024-07-11 |
| PE20250776A1 (en) | 2025-03-14 |
| CO2024009568A2 (en) | 2024-07-29 |
| TW202340215A (en) | 2023-10-16 |
| IL313735A (en) | 2024-08-01 |
| CA3244187A1 (en) | 2023-06-29 |
| WO2023122134A1 (en) | 2023-06-29 |
| US20230192722A1 (en) | 2023-06-22 |
| MX2024007951A (en) | 2024-07-10 |
| EP4452982A1 (en) | 2024-10-30 |
| KR20240136984A (en) | 2024-09-19 |
| CL2024001873A1 (en) | 2024-12-06 |
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